Isonitriles as source and fate of imidoyl radicals: A novel homolytic α-fragmentation

Article abstract of DOI:10.1016/S0040-4039(97)82958-9

Imidoyl radicals 4a-c react with phenylacetylene to give annulation products and nitrile 12, arising from β-scission of the intermediate iminyl radical that is involved in the rearrangement of azaspirocyclohexadienyl 8. In contrast, imidoyls 4d and 15 do not react with the alkyne and give good yields of the corresponding isonitriles through a novel example of homolytic α-fragmentation.